CN103524441A - Compound comprising triazole structure, preparation method thereof and application of compound taken as weed killer - Google Patents
Compound comprising triazole structure, preparation method thereof and application of compound taken as weed killer Download PDFInfo
- Publication number
- CN103524441A CN103524441A CN201310451042.2A CN201310451042A CN103524441A CN 103524441 A CN103524441 A CN 103524441A CN 201310451042 A CN201310451042 A CN 201310451042A CN 103524441 A CN103524441 A CN 103524441A
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- CN
- China
- Prior art keywords
- triazole
- compound
- chloride
- preparation
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 53
- 238000002360 preparation method Methods 0.000 title claims abstract description 39
- 239000004009 herbicide Substances 0.000 title abstract description 6
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 title abstract 3
- 125000001425 triazolyl group Chemical group 0.000 title 1
- -1 acryl Chemical group 0.000 claims abstract description 28
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 12
- 125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 10
- 239000003513 alkali Substances 0.000 claims abstract description 9
- 125000005257 alkyl acyl group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 238000007336 electrophilic substitution reaction Methods 0.000 claims abstract description 9
- 240000006995 Abutilon theophrasti Species 0.000 claims abstract description 4
- 240000001592 Amaranthus caudatus Species 0.000 claims abstract description 4
- 235000009328 Amaranthus caudatus Nutrition 0.000 claims abstract description 4
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims abstract description 4
- 241001645380 Bassia scoparia Species 0.000 claims abstract description 4
- 241000218228 Humulus Species 0.000 claims abstract description 4
- 235000002594 Solanum nigrum Nutrition 0.000 claims abstract description 4
- 240000002307 Solanum ptychanthum Species 0.000 claims abstract description 4
- 235000012735 amaranth Nutrition 0.000 claims abstract description 4
- 239000004178 amaranth Substances 0.000 claims abstract description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 38
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 6
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 6
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 5
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 5
- KYWXRBNOYGGPIZ-UHFFFAOYSA-N 1-morpholin-4-ylethanone Chemical compound CC(=O)N1CCOCC1 KYWXRBNOYGGPIZ-UHFFFAOYSA-N 0.000 claims description 4
- 244000025254 Cannabis sativa Species 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical class O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 claims description 3
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims description 3
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical group ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims description 3
- 241000981770 Buddleja asiatica Species 0.000 claims description 3
- 240000006122 Chenopodium album Species 0.000 claims description 3
- 235000009344 Chenopodium album Nutrition 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 235000007351 Eleusine Nutrition 0.000 claims description 3
- 241000209215 Eleusine Species 0.000 claims description 3
- 241000628997 Flos Species 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 3
- GETTZEONDQJALK-UHFFFAOYSA-N trifluorotoluene Substances FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims description 3
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- KRCSBYPKUJAPSQ-UHFFFAOYSA-N benzene formyl chloride Chemical class C(=O)Cl.C1=CC=CC=C1 KRCSBYPKUJAPSQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- GFAUNYMRSKVDJL-UHFFFAOYSA-N formyl chloride Chemical class ClC=O GFAUNYMRSKVDJL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 abstract description 22
- 150000003852 triazoles Chemical group 0.000 abstract description 15
- 241000196324 Embryophyta Species 0.000 abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 244000025670 Eleusine indica Species 0.000 abstract 2
- 235000014716 Eleusine indica Nutrition 0.000 abstract 2
- 241000448435 Acalypha australis Species 0.000 abstract 1
- 240000006162 Chenopodium quinoa Species 0.000 abstract 1
- 241000207894 Convolvulus arvensis Species 0.000 abstract 1
- 235000001602 Digitaria X umfolozi Nutrition 0.000 abstract 1
- 235000017898 Digitaria ciliaris Nutrition 0.000 abstract 1
- 235000005476 Digitaria cruciata Nutrition 0.000 abstract 1
- 235000006830 Digitaria didactyla Nutrition 0.000 abstract 1
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 abstract 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 abstract 1
- 241001317584 Ixeris chinensis Species 0.000 abstract 1
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 abstract 1
- 241000267237 Viola prionantha Species 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 244000230342 green foxtail Species 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 42
- 238000001816 cooling Methods 0.000 description 42
- 238000003756 stirring Methods 0.000 description 42
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 41
- 238000001556 precipitation Methods 0.000 description 35
- 238000001228 spectrum Methods 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 21
- 238000013019 agitation Methods 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 238000005406 washing Methods 0.000 description 21
- 238000004821 distillation Methods 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 230000002363 herbicidal effect Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 238000009333 weeding Methods 0.000 description 5
- 230000009471 action Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 230000003449 preventive effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RGPBQGGBWIMGMA-BJMVGYQFSA-N 5-[(e)-[5-(4-bromophenyl)-6-hydroxy-3,6-dihydro-1,3,4-oxadiazin-2-ylidene]methyl]-1h-pyrimidine-2,4-dione Chemical compound OC1O\C(=C\C=2C(NC(=O)NC=2)=O)NN=C1C1=CC=C(Br)C=C1 RGPBQGGBWIMGMA-BJMVGYQFSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 2
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- UAGYEVRJKDMCFA-UHFFFAOYSA-N 1-phenyl-3-(1h-1,2,4-triazol-5-yl)urea Chemical compound C=1C=CC=CC=1NC(=O)NC1=NC=NN1 UAGYEVRJKDMCFA-UHFFFAOYSA-N 0.000 description 1
- JBLIDPPHFGWTKU-UHFFFAOYSA-N 2,6-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C=CC=C1Cl JBLIDPPHFGWTKU-UHFFFAOYSA-N 0.000 description 1
- QRHUZEVERIHEPT-UHFFFAOYSA-N 2,6-difluorobenzoyl chloride Chemical compound FC1=CC=CC(F)=C1C(Cl)=O QRHUZEVERIHEPT-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- RAAGZOYMEQDCTD-UHFFFAOYSA-N 2-fluorobenzoyl chloride Chemical compound FC1=CC=CC=C1C(Cl)=O RAAGZOYMEQDCTD-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- QJNGEUXMEXYZNP-UHFFFAOYSA-N 4-methyl-n-(1h-1,2,4-triazol-5-yl)benzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC1=NC=NN1 QJNGEUXMEXYZNP-UHFFFAOYSA-N 0.000 description 1
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
- ZGALGAJAQYISLR-UHFFFAOYSA-N 4-nitro-n-(1h-1,2,4-triazol-5-yl)benzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NC1=NC=NN1 ZGALGAJAQYISLR-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- 0 CC[C@]1C(**)=NN=CC1 Chemical compound CC[C@]1C(**)=NN=CC1 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229950001902 dimevamide Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229940116335 lauramide Drugs 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000013332 literature search Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- XGLLDHTXWOIYCZ-UHFFFAOYSA-N n-(1h-1,2,4-triazol-5-yl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC1=NC=NN1 XGLLDHTXWOIYCZ-UHFFFAOYSA-N 0.000 description 1
- HXIZGGAFQSNQAD-UHFFFAOYSA-N n-(1h-1,2,4-triazol-5-yl)pentanamide Chemical compound CCCCC(=O)NC1=NC=NN1 HXIZGGAFQSNQAD-UHFFFAOYSA-N 0.000 description 1
- YZDOTVLVWXHISA-UHFFFAOYSA-N n-(1h-1,2,4-triazol-5-yl)propanamide Chemical compound CCC(=O)NC1=NC=NN1 YZDOTVLVWXHISA-UHFFFAOYSA-N 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
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Abstract
The invention discloses a compound comprising a triazole structure, a preparation method thereof and an application of the compound taken as a weed killer. The structure formula of the compound comprising the triazole structure is shown in a formula I, R represents allyl, alkyl acyl with a carbon atom number of 1-20, substituted or un-substituted benzoyl, O, O-dimethyl phosphoroamido-thioate, phenyl, benzene oxygen acetyl, 3-phenyl-2 acryl or 2, 6-binitro-4-trifluoro methyl phenyl. The preparation method of the compound shown in the formula I comprises the steps as follows: under the catalytic action of alkali, 3-amino-1 H-1, 2, 4-triazole and an electrophilic reagent are subjected to electrophilic substitution reaction, so that the compound shown in the formula I is obtained. The weed killer can be used for preventing and killing weeds, green bristle grass, crab grass, eleusine indica, black nightshade, amaranth, piemarker, quinoa, scandent hop, summer cypress, field bindweed, acalypha australis, Ixeris chinensis and viola prionantha.
Description
Technical field
The present invention relates to a kind of compound containing triazole structure and preparation method thereof and application as weedicide, belong to chemistry of pesticide field.
Background technology
At present, the research and development emphasis of chemical pesticide is design and the screening that contains aromatic ring, heterocycle and fused ring compound.There are different bioactive groups and be combined in same molecule, can realize bioactive stack or enhancing.Triazole class compounds has good biological activity, and it has the plurality of advantages such as active high and low poison, wide spectrum, interior suction conductivity be good as sterilant, sterilant, miticide.After U.S. FMC, Tao Shi benefit agriculture, Japanese Wu Yu chemistry and Japanese Chugai Deng Ji company develop triazole herbicide, triazole class compounds is carried out to structure of modification and the research that obtains novel herbicidal compound has become a new focus.Because traditional triazole herbicide herbicide spectrum is narrow, speed of action is slow, dosage is large; therefore other some active groups (as halogen-containing benzoyl, benzene oxygen ethanoyl etc.) are introduced in triazole class compounds, can be obtained efficient, lasting novel herbicidal compound.According to high flux screening principle, often a series of active groups are introduced in triazole class compounds, to increasing the action target site of new compound, improve weeding activity and speed of action, reduce consumption.By literature search, US Patent No. 3144460 has been announced a kind of 1,2 of urea groups that contains, the synthetic and biological activity of 4-triazole derivative.The periodicals such as " Central China Normal University's journal (natural science edition) " the 33rd volume the 3rd phase 383-386, " organic chemistry " the 28th volume the 6th phase 1065-1070, " organic chemistry " the 29th volume second phase 245-251 in 2009 in 2008 in 1999 have reported 1, the research of the synthetic and weeding activity of 2,4-triazole derivative; Patent CN102775361, JPH0341072, JPH05163253, JPH05163254, JPS5998004 etc. have all announced 1,2, the synthetic and weeding activity of 4-triazole derivative.Along with becoming increasingly conspicuous of Weed Resistance problem, the weedicide new variety of novel structure, mechanism of action uniqueness become the active demand in market, and the triazole class compounds of therefore take is developed its herbicidal compound containing several functions group as parent and will be had good prospect.
Summary of the invention
The object of this invention is to provide a kind of compound containing triazole structure and preparation method thereof and application as weedicide.
Compound shown in formula I provided by the present invention,
In formula I, R represents alkyl acyl, replacement or unsubstituted benzoyl, the O that allyl group, carbonatoms are 1～20, O-dimethyl thiophosphoryl, phenyl, benzene oxygen ethanoyl, 3-phenyl-2-acryl or 2,6-dinitrobenzene-4-trifluoromethyl.
In above-mentioned compound, the carbonatoms of described alkyl acyl can be 3～18, as propionyl, butyryl radicals, pentanoyl, caproyl, lauroyl or stearoyl;
The benzoyl of described replacement can be single-substituted formyl radical or disubstituted benzene formyl radical; substituting group in the benzoyl of described replacement can be fluorine, chlorine, nitro or methyl; as 2-chlorobenzene formacyl, 4-chlorobenzene formacyl, 2; 6-dichloro-benzoyl base, 2-fluoro benzoyl, 4-fluoro benzoyl, 2,6-difluoro benzoyl, 4-nitro benzoyl or 4-methyl benzoyl.
The preparation method who the present invention further provides compound shown in formula I, comprises the steps:
Under the katalysis of alkali, 3-amino-1H-1,2,4-triazole and electrophilic reagent obtain compound shown in formula I through electrophilic substitution reaction;
Described electrophilic reagent is alkyl acyl chloride, replacement or unsubstituted Benzoyl chloride, the O that chlorallylene, carbonatoms are 1～20, O-dimethyl thiophosphoryl chloride, phenyl isocyanate, phenoxyacetyl chloride, 3-phenyl-2-acrylate chloride or 4-are chloro-3,5-dinitro-p-trifluorotoluene.
In above-mentioned preparation method, the carbonatoms of described alkyl acyl chloride can be 3～18, specifically can be propionyl chloride, butyryl chloride, valeryl chloride, caproyl chloride, lauroyl chloride or stearoyl chlorine;
The benzoyl of described replacement can be single-substituted formyl chloride or disubstituted benzene formyl chloride, substituting group in the Benzoyl chloride of described replacement can be fluorine, chlorine, nitro or methyl, specifically can be Benzoyl chloride, 2-chloro-benzoyl chloride, 4-chloro-benzoyl chloride, 2,6-dichlorobenzoyl chloride, 2-fluorobenzoyl chloride, 4-fluorobenzoyl chloride, 2,6-difluoro benzoyl chloride, 4-nitrobenzoyl chloride or 4-methyl benzoyl chloride.
In above-mentioned preparation method, described alkali can be pyridine, triethylamine, Tri-n-Propylamine, tri-n-butylamine, N, N-diisopropylethylamine, DMAP, Tetramethyl Ethylene Diamine, 1,8-diazabicylo [5.4.0] 11 carbon-7-alkene (DBU), 1,5-diazabicylo [4.3.0] ninth of the ten Heavenly Stems-5-alkene (DBN), 1, in 5,7-, tri-azabicyclics [4.4.0] last of the ten Heavenly stems-5-alkene (TBD) at least one;
The solvent of described electrophilic substitution reaction can be at least one in dimethyl formamide, pyridine, tetrahydrofuran (THF), acetone, butanone, pimelinketone, dioxane, methylnaphthalene, dimethyl sulfoxide (DMSO), toluene, dimethylbenzene, methylene dichloride, ethylene dichloride, chloroform, hexanaphthene, hexane, phenyl ether, tetracol phenixin, N-Methyl pyrrolidone, N-formyl morpholine and N-ethanoyl morpholine.
In above-mentioned preparation method, described electrophilic reagent is dissolved in the solvent of described electrophilic substitution reaction and obtains solution, described solution is added drop-wise to by described 3-amino-1H-1, in the system that 2,4-triazole, described solvent and described alkali form;
Before dripping described solution, described system can be cooled to-5～15 ℃, specifically can be-5～11 ℃ ,-5 ℃ ,-4 ℃ ,-3 ℃, 0 ℃, 1 ℃, 3 ℃, 6 ℃, 7 ℃, 8 ℃, 10 ℃, 11 ℃ or 15 ℃.
In above-mentioned preparation method, described 3-amino-1H-1, 2, 4-triazole, the mol ratio of described alkali and described electrophilic reagent can be 1.0:1.5～8:0.8～1.5, specifically can be 1.0:1.5～6:0.8～1.2, 1.0:1.5:0.8, 1.0:1.5:0.9, 1.0:1.5:1.1, 1.0:1.5:1.2, 1.0:2.0:0.8, 1.0:2.0:1.0, 1.0:2.0:1.1, 1.0:3.0:0.9, 1.0:3.0:1.0, 1.0:3.0:1.2, 1.0:4.0:1.1, 1.0:4.0:1.2, 1.0:4.0:1.5, 1.0:6.0:0.8, 1.0:6.0:1.3, 1.0:6.0:1.4, 1.0:6.0:1.5, 1.0:7.0:1.2, 1.0:7.0:1.5 or 1.0:8.0:1.1, 1:8:1,
Shown in the temperature of electrophilic substitution reaction be 20 ℃～30 ℃, the time is 4～7 hours, specifically can be 4～7 hours, 4 hours, 5 hours, 6 hours or 7 hours.
The present invention also provides compound shown in formula I in the application as in weedicide.
The present invention also further provides a kind of weedicide, and its activeconstituents is compound shown in formula I.
Weedicide provided by the invention can be used for management of weeds dog tail, lady's-grass, Herba Eleusines Indicae, black nightshade, three-coloured amaranth, piemarker, lamb's-quarters, humulus grass, summer cypress, Herba seu Flos Convolvuli arvensis, Herba Acalyphae, Herba Ixeritis chinensis and early opens violet.
Herbicidal compound containing triazole structure provided by the invention, its novel structure, has the plurality of advantages such as activity is high, broad weed-killing spectrum, has good weeding activity.Preparation method provided by the invention, technique is simple, and reaction mechanism is shorter.
Embodiment
The experimental technique using in following embodiment if no special instructions, is ordinary method.
In following embodiment, material used, reagent etc., if no special instructions, all can obtain from commercial channels.
The structural formula of following embodiment electrophilic reagent used is as shown in table 1.
The structural formula of table 1 electrophilic reagent
"--" representative is blank herein.
Embodiment 1, preparation Compound C 1(3-allyl amino-4H-1,2,4-triazole)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the triethylamine of 2,4-triazole, 50ml dimethyl formamide and 0.04mol, cooling and stirring to system temperature is 3 ℃; To the dimethyl formamide solution that dropwise adds 0.012mol chlorallylene in four-hole bottle, after dropping finishes, stirring at normal temperature reaction 7h, after underpressure distillation precipitation, with methylene dichloride, dissolve, separatory after washing, gets oil reservoir, revolve and steam recrystallizing methanol after precipitation, obtain Compound C 1, productive rate is 71.4%, and purity is 99.1%.
3-allyl amino-4H-1, the carbon spectrum data of 2,4-triazole
13c NMR(CDCl
3) δ
ppm=54.5,114.9,134.3,148.1,158.3.
Through characterizing, it is target compound.
Embodiment 2, preparation Compound C 2(N-(4H-[1,2,4] triazole-3-yl)-propionic acid amide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the tri-n-butylamine of 2,4-triazole, 50ml dimethyl sulfoxide (DMSO) and 0.06mol, cooling and stirring to system temperature is 10 ℃; To the acetonitrile solution that dropwise adds 0.014mol propionyl chloride in four-hole bottle, after dripping and finishing, stirring at normal temperature reaction 4h, dissolves with methylene dichloride after underpressure distillation precipitation, washing, separatory is got oil reservoir, revolves and steams recrystallizing methanol after precipitation, obtain Compound C 2, productive rate is 73.7%, and purity is 98.5%.
N-(4H-[1,2,4] triazole-3-yl) the carbon spectrum data of-propionic acid amide
13c NMR(CDCl
3) δ
ppm=9.7,26.7,148.0,158.4,172.7.
Through characterizing, it is target compound.
Embodiment 3, preparation Compound C 3(N-(4H-[1,2,4] triazole-3-yl)-butyramide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the pyridine of 2,4-triazole, 50ml pimelinketone and 0.08mol, cooling and stirring to system temperature is 15 ℃; To the pimelinketone solution that dropwise adds 0.011mol butyryl chloride in four-hole bottle, after dripping and finishing, stirring at normal temperature reaction 4h, dissolves with methylene dichloride after underpressure distillation precipitation, washing, separatory is got oil reservoir, revolves and steams recrystallizing methanol after precipitation, obtain Compound C 3, productive rate is 70.2%, and purity is 99.6%.
N-(4H-[1,2,4] triazole-3-yl) the carbon spectrum data of-butyramide
13c NMR(CDCl
3) δ
ppm=13.0,18.8,36.1,148.2,158.1,172.0.
Through characterizing, it is target compound.
Embodiment 4, preparation Compound C 4(N-(4H-[1,2,4] triazole-3-yl)-valeramide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the Tetramethyl Ethylene Diamine of 2,4-triazole, 50ml methylnaphthalene and 0.06mol, cooling and stirring to system temperature is 8 ℃; To the dichloromethane solution that dropwise adds 0.014mol valeryl chloride in four-hole bottle, after dripping and finishing, stirring at normal temperature reaction 6h, separatory after washing, gets oil reservoir, and recrystallizing methanol after underpressure distillation precipitation, obtains Compound C 4, and productive rate is 66.3%, and purity is 99.2%.
N-(4H-[1,2,4] triazole-3-yl) the carbon spectrum data of-valeramide
13c NMR(CDCl
3) δ
ppm=13.322.128.233.6148.2158.5172.2.
Embodiment 5, preparation Compound C 5(N-(4H-[1,2,4] triazole-3-yl)-hexanamide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the DMAP of 2,4-triazole, 50ml pyridine and 0.03mol, cooling and stirring to system temperature is-3 ℃; To the acetonitrile solution that dropwise adds 0.01mol caproyl chloride in four-hole bottle, after dripping and finishing, stirring at normal temperature reaction 5h, dissolves with methylene dichloride after decompression precipitation, washing, separatory is got oil reservoir, revolves and steams recrystallizing methanol after precipitation, obtain Compound C 5, productive rate is 70.5%, and purity is 99.8%.
N-(4H-[1,2,4] triazole-3-yl) the carbon spectrum data of-hexanamide
13c NMR(CDCl
3) δ
ppm=14.0,22.4,25.7,31.5,33.9,148.3,158.0,171.9.
Through characterizing, it is target compound.
Embodiment 6, preparation Compound C 6(N-(4H-[1,2,4] triazole-3-yl)-lauramide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the Tri-n-Propylamine of 2,4-triazole, 50ml toluene and 0.06mol, cooling and stirring to system temperature is 8 ℃; To the toluene solution that dropwise adds 0.013mol lauroyl chloride in four-hole bottle, after dripping and finishing, stirring at normal temperature reaction 6h, separatory after washing, gets oil reservoir, revolves and steams recrystallizing methanol after precipitation, obtains Compound C 6, and productive rate is 68.6%, and purity is 99.4%.
N-(4H-[1,2,4] triazole-3-yl) the carbon spectrum data of-lauramide
13c NMR(CDCl
3) δ
ppm=14.0,23.1,26.0,29.3,29.6,30.0,30.1,30.2,30.3,32.5,33.9,148.2,158.4,170.1.
Through characterizing, it is target compound.
Embodiment 7, preparation Compound C 7(N-(4H-[1,2,4] triazole-3-yl)-stearylamide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the TBD of 2,4-triazole, 50ml dimethylbenzene and 0.015mol, cooling and stirring to system temperature is-5 ℃; To the xylene solution that dropwise adds 0.009mol stearoyl chlorine in four-hole bottle, after dripping and finishing, stirring at normal temperature reaction 7h, separatory after washing, gets oil reservoir, and recrystallizing methanol after underpressure distillation precipitation, obtains Compound C 7, and productive rate is 70.1%, and purity is 99.0%.
N-(4H-[1,2,4] triazole-3-yl) the carbon spectrum data of-stearylamide
13c NMR(CDCl
3) δ
ppm=14.1,23.2,26.0,29.2,29.5,30.0,30.1,30.2,30.3,30.3,30.3,30.3,30.3,30.3,30.3,30.3,33.9,148.1,158.4,172.0.
Through characterizing, it is target compound.
Embodiment 8, preparation Compound C 8(N-(4H-[1,2,4] triazole-3-yl)-O, O '-dimethyl thiophosphoryl amide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the Tetramethyl Ethylene Diamine of 2,4-triazole, 50ml N-ethanoyl morpholine and 0.04mol, cooling and stirring to system temperature is-4 ℃; In four-hole bottle, dropwise add 0.011mol O, the acetone soln of O-dimethyl thiophosphoryl chloride, after dropping finishes, stirring at normal temperature reaction 6h, dissolves with methylene dichloride after underpressure distillation precipitation, washing, separatory is got oil reservoir, revolves and steams recrystallizing methanol after precipitation, obtains chemical combination C8, productive rate is 69.5%, and purity is 99.6%.
N-(4H-[1,2,4] triazole-3-yl)-O, the carbon spectrum data of O '-dimethyl thiophosphoryl amide
13c NMR(CDCl
3) δ
ppm=40.2,40.3,148.2,158.4.
Through characterizing, it is target compound.
Embodiment 9, preparation Compound C 9(1-phenyl-3-(4H-[1,2,4] triazole-3-yl)-urea)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the DBU of 2,4-triazole, 50ml butanone and 0.03mol, cooling and stirring to system temperature is 6 ℃; To the dichloroethane solution that dropwise adds 0.012mol phenyl isocyanate in four-hole bottle, after dripping and finishing, stirring at normal temperature reaction 5h, washing, separatory is got oil reservoir, revolves and steams recrystallizing methanol after precipitation, obtains Compound C 9, and productive rate is 68.8%, and content is 98.8%.
1-phenyl-3-(4H-[1,2,4] triazole-3-yl) the carbon spectrum data of-urea
13c NMR(CDCl
3) δ
ppm=120.3,120.4,124.1,128.6,128.7,138.2,148.3,152.2,158.4.
Through characterizing, it is target compound.
Embodiment 10, preparation Compound C 10(N-(4H-[1,2,4] triazole-3-yl)-benzamide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the triethylamine of 2,4-triazole, 50ml dioxane and 0.06mol, cooling and stirring to system temperature is 0 ℃; To the tetrahydrofuran solution that dropwise adds 0.015mol Benzoyl chloride in four-hole bottle, after dripping and finishing, stirring at normal temperature reaction 6h, revolves after steaming precipitation and dissolves with methylene dichloride, washing, separatory is got oil reservoir, revolves and steams recrystallizing methanol after precipitation, obtain Compound C 10, productive rate is 71.9%, and purity is 99.4%.
N-(4H-[1,2,4] triazole-3-yl) the carbon spectrum data of-benzamide
13c NMR(CDCl
3) δ
ppm=127.3,127.4,128.5,128.6,131.9,133.5,148.1,158.2,165.2.
Through characterizing, it is target compound.
Embodiment 11, the chloro-N-(4H-[1 of preparation Compound C 11(2-, 2,4] triazole-3-yl)-benzamide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the DBN of 2,4-triazole, 50ml pimelinketone and 0.02mol, cooling and stirring to system temperature is 11 ℃; To the acetone soln that dropwise adds 0.011mol2-chloro-benzoyl chloride in four-hole bottle, after dripping and finishing, stirring at normal temperature reaction 4h, dissolves with methylene dichloride after underpressure distillation precipitation, washing, separatory is got oil reservoir, revolves and steams recrystallizing methanol after precipitation, obtain Compound C 11, productive rate is 68.6%, and purity is 98.7%.
The chloro-N-(4H-[1 of 2-, 2,4] triazole-3-yl) the carbon spectrum data of-benzamide
13c NMR(CDCl
3) δ
ppm=126.7,128.7,129.0,132.6,133.3,133.9,148.2,158.5,165.3.
Embodiment 12, the chloro-N-(4H-[1 of preparation Compound C 12(4-, 2,4] triazole-3-yl)-benzamide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the tri-n-butylamine of 2,4-triazole, 50ml hexanaphthene and 0.07mol, cooling and stirring to system temperature is 7 ℃; To the carbon tetrachloride solution that dropwise adds 0.015mol4-chloro-benzoyl chloride in four-hole bottle, after dripping and finishing, stirring at normal temperature reaction 4h, separatory after washing, gets oil reservoir, and recrystallizing methanol after underpressure distillation precipitation, obtains Compound C 12, and productive rate is 66.5%, and purity is 99.6%.
The chloro-N-(4H-[1 of 4-, 2,4] triazole-3-yl) the carbon spectrum data of-benzamide
13c NMR(CDCl
3) δ
ppm=128.5,128.7,129.0,129.1,131.6,137.2,148.1,158.3,165.1.
Through characterizing, it is target compound.
Embodiment 13, preparation Compound C 13(2, the chloro-N-(4H-[1 of 6-bis-, 2,4] triazole-3-yl)-benzamide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the pyridine of 2,4-triazole, 50ml dimethyl formamide and 0.07mol, cooling and stirring to system temperature is 6 ℃; In four-hole bottle, dropwise add 0.012mol2, the dimethyl formamide solution of 6-dichlorobenzoyl chloride, after dropping finishes, stirring at normal temperature reaction 6h, dissolves with methylene dichloride after underpressure distillation precipitation, washing, separatory is got oil reservoir, revolves and steams recrystallizing methanol after precipitation, obtains Compound C 13, productive rate is 72.8%, and purity is 99.7%.
The chloro-N-(4H-[1 of 2,6-bis-, 2,4] triazole-3-yl) the carbon spectrum data of-benzamide
13c NMR(CDCl
3) δ
ppm=127.1,127.2,134.1,134.2,134.3,134.7,148.5,158.3,165.2.
Through characterizing, it is target compound.
Embodiment 14, the fluoro-N-(4H-[1 of preparation Compound C 14(4-, 2,4] triazole-3-yl)-benzamide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the DBU of 2,4-triazole, 50ml chloroform and 0.04mol, cooling and stirring to system temperature is-3 ℃; To the chloroformic solution that dropwise adds 0.015mol4-fluorobenzoyl chloride in four-hole bottle, after dripping and finishing, stirring at normal temperature reaction 5h, separatory after washing, gets oil reservoir, revolves and steams recrystallizing methanol after precipitation, obtains Compound C 14, and productive rate is 74.4%, and purity is 99.3%.
The fluoro-N-(4H-[1 of 4-, 2,4] triazole-3-yl) the carbon spectrum data of-benzamide
13c NMR(CDCl
3) δ
ppm=115.6,115.7,128.8,128.9,129.1,148.2,158.3,165.1,165.5.
Through characterizing, it is target compound.
Embodiment 15, the fluoro-N-(4H-[1 of preparation Compound C 15(2-, 2,4] triazole-3-yl)-benzamide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the pyridine of 2,4-triazole, 50ml phenyl ether and 0.06mol, cooling and stirring to system temperature is 3 ℃; To the hexane solution that dropwise adds 0.012mol2-fluorobenzoyl chloride in four-hole bottle, after dripping and finishing, stirring at normal temperature reaction 4h, separatory after washing, gets oil reservoir, and recrystallizing methanol after underpressure distillation precipitation, obtains Compound C 15, and productive rate is 69.6%, and purity is 99.3%.
The fluoro-N-(4H-[1 of 2-, 2,4] triazole-3-yl) the carbon spectrum data of-benzamide
13c NMR(CDCl
3) δ
ppm=115.6,120.5,124.2,128.9,133.5,148.1,158.2,160.9,165.2.
Embodiment 16, preparation Compound C 16(2, the fluoro-N-(4H-[1 of 6-bis-, 2,4] triazole-3-yl)-benzamide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the TBD of 2,4-triazole, 50ml N-Methyl pyrrolidone and 0.015mol, cooling and stirring to system temperature is-3 ℃; In four-hole bottle, dropwise add 0.012mol2, the acetonitrile solution of 6-difluoro benzoyl chloride, after dropping finishes, stirring at normal temperature reaction 4h, dissolves with methylene dichloride after underpressure distillation precipitation, washing, separatory is got oil reservoir, revolves and steams recrystallizing methanol after precipitation, obtains Compound C 16, productive rate is 66.9%, and purity is 99.3%.
The fluoro-N-(4H-[1 of 2,6-bis-, 2,4] triazole-3-yl) the carbon spectrum data of-benzamide
13c NMR(CDCl
3) δ
ppm=107.5,111.1,111.2,135.1,148.1,158.3,162.4,162.5,165.2.
Through characterizing, it is target compound.
Embodiment 17, preparation Compound C 17(4-nitro-N-(4H-[1,2,4] triazole-3-yl)-benzamide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, 2, the DIPEA of 4-triazole, 50ml N-ethanoyl morpholine and 0.06mol, cooling and stirring to system temperature is 10 ℃; To the acetone soln that dropwise adds 0.008mol4-nitrobenzoyl chloride in four-hole bottle, after dropping finishes, stirring at normal temperature reaction 5h, after underpressure distillation precipitation, with methylene dichloride, dissolve, washing, separatory is got oil reservoir, revolve and steam recrystallizing methanol after precipitation, obtain Compound C 17, productive rate is 69.4%, and purity is 99.7%.
4-nitro-N-(4H-[1,2,4] triazole-3-yl) the carbon spectrum data of-benzamide
13c NMR(CDCl
3) δ
ppm=123.6,123.7,128.1,128.2,139.6,148.2,151.8,158.4,165.2.
Through characterizing, it is target compound.
Embodiment 18, preparation Compound C 18(4-methyl-N-(4H-[1,2,4] triazole-3-yl)-benzamide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the DBU of 2,4-triazole, 50ml N-formyl morpholine and 0.03mol, cooling and stirring to system temperature is 1 ℃; To the tetrahydrofuran solution that dropwise adds 0.012mol4-methyl benzoyl chloride in four-hole bottle, after dropping finishes, stirring at normal temperature reaction 7h, after underpressure distillation precipitation, with methylene dichloride, dissolve, washing, separatory is got oil reservoir, revolve and steam recrystallizing methanol after precipitation, obtain Compound C 18, productive rate is 65.6%, and purity is 99.4%.
4-methyl-N-(4H-[1,2,4] triazole-3-yl) the carbon spectrum data of-benzamide
13c NMR(CDCl
3) δ
ppm=20.9,127.1,127.2,129.3,129.4,130.5,141.1,148.1,158.4,165.1.
Through characterizing, it is target compound.
Embodiment 19, preparation Compound C 19(2-phenoxy group-N-(4H-[1,2,4] triazole-3-yl)-ethanamide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the tri-n-butylamine of 2,4-triazole, 50ml dimethyl sulfoxide (DMSO) and 0.08mol, cooling and stirring to system temperature is 7 ℃; To the dichloromethane solution that dropwise adds 0.011mol phenoxyacetyl chloride in four-hole bottle, after dropping finishes, stirring at normal temperature reaction 5h, after underpressure distillation precipitation, with methylene dichloride, dissolve, washing, separatory is got oil reservoir, revolve and steam recrystallizing methanol after precipitation, obtain Compound C 19, productive rate is 73.3%, and purity is 99.1%.
2-phenoxy group-N-(4H-[1,2,4] triazole-3-yl) the carbon spectrum data of-ethanamide
13c NMR(CDCl
3) δ
ppm=75.9,114.0,114.1,120.8,129.5,129.6,148.1,158.3,162.0,168.2.
Through characterizing, it is target compound.
Embodiment 20, preparation Compound C 20(3-phenyl-N-(4H-[1,2,4] triazole-3-yl)-acrylamide)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the triethylamine of 2,4-triazole, 50ml pyridine and 0.02mol, cooling and stirring to system temperature is 3 ℃; To the acetonitrile solution that dropwise adds 0.01mol3-phenyl-2-acrylate chloride in four-hole bottle, after dropping finishes, stirring at normal temperature reaction 5h, after underpressure distillation precipitation, with methylene dichloride, dissolve, washing, separatory is got oil reservoir, revolve and steam recrystallizing methanol after precipitation, obtain Compound C 20, productive rate is 74.4%, and purity is 99.8%.
3-phenyl-N-(4H-[1,2,4] triazole-3-yl) the carbon spectrum data of-acrylamide
13c NMR(CDCl
3) δ
ppm=119.8,126.1,126.2,127.7,128.3,128.4,134.9,141.6,148.3,158.4,163.8.
Embodiment 21, preparation Compound C 21((2,6-dinitrobenzene-4-trifluoromethyl-phenyl)-(4H-[1,2,4] triazole-3-yl)-amine)
To the 3-amino-1H-1 that adds 0.01mol in the 250ml four-hole bottle with magnetic agitation, cooling, thermometer, nitrogen protection, the pyridine of 2,4-triazole, 50ml dimethyl formamide and 0.08mol, cooling and stirring to system temperature is 15 ℃; In four-hole bottle, dropwise add 0.01mol4-chloro-3, the tetrahydrofuran solution of 5-dinitro-p-trifluorotoluene, after dropping finishes, stirring at normal temperature reaction 7h, dissolves with methylene dichloride after underpressure distillation precipitation, washing, separatory is got oil reservoir, revolves and steams recrystallizing methanol after precipitation, obtains Compound C 21, productive rate is 71.6%, and purity is 99.5%.
The carbon spectrum data of (2,6-dinitrobenzene-4-trifluoromethyl-phenyl)-(4H-[1,2,4] triazole-3-yl)-amine
13c NMR(CDCl
3) δ
ppm=117.3,122.8,127.3,127.4,136.1,136.2,140.2,148.1,158.4.
Through characterizing, it is target compound.
The weeding activity of embodiment 22, Compound C 1-Compound C 21
Choose wild grassland and carry out the test of pesticide effectiveness, evaluate the drug effect containing triazole structure herbicidal compound C1-C21 of above-mentioned preparation.
The spraying medicine concentration of every kind of compound is respectively 500mg/L and 1000mg/L, and each concentration is established 3 processing, averages, and each processing area is 10m
2, and corresponding clear water contrast is set.Within after dispenser 14 days, investigate its fresh weight preventive effect to weeds.
Fresh weight preventive effect
(G
0for certain weeds fresh weight of clear water check plot, G is certain weeds fresh weight of chemicals treatment district).
Statistics is as shown in table 2.
The fresh weight preventive effect of table 2 Compound C 1-C21 to different sorts weeds
"--" represents in set experiment community does not have this grass.
By the data in table 2, can be learnt, triazole class compounds provided by the invention has certain inhibition activity to opening weeds dog tail, lady's-grass, Herba Eleusines Indicae, black nightshade, three-coloured amaranth, piemarker, lamb's-quarters, humulus grass, summer cypress, Herba seu Flos Convolvuli arvensis, Herba Acalyphae, Herba Ixeritis chinensis and morning violet.
Claims (10)
1. compound shown in formula I,
In formula I, R represents alkyl acyl, replacement or unsubstituted benzoyl, the O that allyl group, carbonatoms are 1～20, O-dimethyl thiophosphoryl, phenyl, benzene oxygen ethanoyl, 3-phenyl-2-acryl or 2,6-dinitrobenzene-4-trifluoromethyl.
2. compound according to claim 1, is characterized in that:
The carbonatoms of described alkyl acyl is 3～18;
The benzoyl of described replacement is single-substituted formyl radical or disubstituted benzene formyl radical, and the substituting group in the benzoyl of described replacement is fluorine, chlorine, nitro or methyl.
3. the preparation method of compound shown in formula I, comprises the steps:
Under the katalysis of alkali, 3-amino-1H-1,2,4-triazole and electrophilic reagent obtain compound shown in formula I through electrophilic substitution reaction;
Described electrophilic reagent is alkyl acyl chloride, replacement or unsubstituted Benzoyl chloride, the O that chlorallylene, carbonatoms are 1～20, O-dimethyl thiophosphoryl chloride, phenyl isocyanate, phenoxyacetyl chloride, 3-phenyl-2-acrylate chloride or 4-are chloro-3,5-dinitro-p-trifluorotoluene.
4. preparation method according to claim 3, is characterized in that: the carbonatoms of described alkyl acyl chloride is 3～18;
The benzoyl of described replacement is single-substituted formyl chloride or disubstituted benzene formyl chloride, and the substituting group in the Benzoyl chloride of described replacement is fluorine, chlorine, nitro or methyl.
5. according to the preparation method described in claim 3 or 4, it is characterized in that:
Described alkali is pyridine, triethylamine, Tri-n-Propylamine, tri-n-butylamine, N, N-diisopropylethylamine, DMAP, Tetramethyl Ethylene Diamine, 1,8-diazabicylo [5.4.0] 11 carbon-7-alkene, 1,5-diazabicylo [4.3.0] ninth of the ten Heavenly Stems-5-alkene and 1, in 5,7-, tri-azabicyclics [4.4.0] last of the ten Heavenly stems-5-alkene at least one;
The solvent of described electrophilic substitution reaction is at least one in dimethyl formamide, pyridine, tetrahydrofuran (THF), acetone, butanone, pimelinketone, dioxane, methylnaphthalene, dimethyl sulfoxide (DMSO), toluene, dimethylbenzene, methylene dichloride, ethylene dichloride, chloroform, hexanaphthene, hexane, phenyl ether, tetracol phenixin, N-Methyl pyrrolidone, N-formyl morpholine and N-ethanoyl morpholine.
6. according to the preparation method described in any one in claim 3-5, it is characterized in that: described electrophilic reagent is dissolved in the solvent of described electrophilic substitution reaction and obtains solution, described solution is added drop-wise to by described 3-amino-1H-1, in the system that 2,4-triazole, described solvent and described alkali form;
Before dripping described solution, described system is cooled to-5～15 ℃.
7. according to the preparation method described in any one in claim 3-6, it is characterized in that: described 3-amino-1H-1, the mol ratio of 2,4-triazole, described alkali and described electrophilic reagent is 1.0:1.5～8:0.8～1.5;
Shown in the temperature of electrophilic substitution reaction be 20 ℃～30 ℃, the time is 4～7 hours.
8. compound shown in formula I is in the application as in weedicide.
9. a weedicide, its activeconstituents is compound shown in formula I described in claim 1 or 2.
10. application according to claim 8 or weedicide claimed in claim 9, is characterized in that: open described weedicide management of weeds dog tail, lady's-grass, Herba Eleusines Indicae, black nightshade, three-coloured amaranth, piemarker, lamb's-quarters, humulus grass, summer cypress, Herba seu Flos Convolvuli arvensis, Herba Acalyphae, Herba Ixeritis chinensis and morning violet.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108402064A (en) * | 2018-04-14 | 2018-08-17 | 张汝伟 | A kind of secondary amine derivative is applied with halosulfuronmethyl synergy and its herbicidal formulations |
| CN108432777A (en) * | 2018-04-14 | 2018-08-24 | 张汝伟 | A kind of secondary amine derivative combines the application in plant growth regulating with TrinexAN_SNacethyl |
| CN108432776A (en) * | 2018-04-14 | 2018-08-24 | 张汝伟 | A kind of composition comprising TrinexAN_SNacethyl and its application in plant growth regulating |
| WO2022008923A1 (en) | 2020-07-10 | 2022-01-13 | MOA Technology Limited | Herbicidal heterocyclic derivatives |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2953491A (en) * | 1957-11-21 | 1960-09-20 | American Cyanamid Co | Fungicide |
| US4416683A (en) * | 1980-09-16 | 1983-11-22 | Eli Lilly And Company | Benzamides, compositions and agricultural method |
| US20090203215A1 (en) * | 2008-02-13 | 2009-08-13 | Fujifilm Corporation | Metal polishing slurry and chemical mechanical polishing method |
-
2013
- 2013-09-27 CN CN201310451042.2A patent/CN103524441B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2953491A (en) * | 1957-11-21 | 1960-09-20 | American Cyanamid Co | Fungicide |
| US4416683A (en) * | 1980-09-16 | 1983-11-22 | Eli Lilly And Company | Benzamides, compositions and agricultural method |
| US20090203215A1 (en) * | 2008-02-13 | 2009-08-13 | Fujifilm Corporation | Metal polishing slurry and chemical mechanical polishing method |
Non-Patent Citations (9)
| Title |
|---|
| A. RICCI1,ET AL.: "Cytokinin-like activity of N′-substituted N-phenylureas", 《PLANT GROWTH REGULATION》, vol. 34, 31 December 2001 (2001-12-31), pages 167 - 172 * |
| ACS: "RN 5295-36-3,5295-25-0,21051-23-0,53497-38-4,90626-45-2,290834-96-7,18385-07-4", 《STN REGISTRY》, 26 September 2000 (2000-09-26) * |
| FREDERICK KURZER ET AL.: "Heterocyclic Compounds from Urea Derivatives. PartⅦ Addition-products of Diaminoguanidine and Carbodi-imides, and their Cyclisation", 《KURZER AND DOURAGHI- ZADEH : HETEROCYCLIC》, 1 January 1965 (1965-01-01), pages 3912 - 3922 * |
| G. N. LIPUNOVA, ET AL.: "Fluorine-Containing Heterocycles: XII. *Fluorine-Containing Quinazolin-4-ones and Azolo[a]quinazolinone Derivatives", 《RUSSIAN JOURNAL OF ORGANIC CHEMISTRY》, vol. 41, no. 7, 31 December 2005 (2005-12-31), pages 1071 - 1080 * |
| G.A.WHITE: "Substituted 2-methylbenzanilides and structurally related carboxamides:inhibition of complexⅡ activity in mitochondria from a wild-type strain and a carboxin-resistant mutant strain of ustilago maydis", 《PESTIDIDE BIOCHEMISTRY AND PHYSIOLOGY》, vol. 34, 31 December 1989 (1989-12-31), pages 255 - 276, XP024867805, DOI: doi:10.1016/0048-3575(89)90165-X * |
| HONGBO CHAI, ET AL.: "Functional properties of synthetic N-acyl-L-homoserine lactone analogs of quorum-sensing gram-negative bacteria on the growth of human oral squamous carcinoma cells", 《INVEST NEW DRUGS》, vol. 30, 28 September 2010 (2010-09-28), pages 157 - 163 * |
| M.SPITELLER ET AL: "Analysis of the binding of amitrole and anilazine to aquatic and terrestrial refractory organic substances", 《MOLECULAR INTERACTIONS》, 31 December 2002 (2002-12-31), pages 446 - 474, XP009157552, DOI: doi:10.1002/9783527611195.ch4e * |
| MASAHARU HAZAWA, ET AL.: "Caspase-independent apoptosis induction of quorum-sensing autoinducer analogs against chronic myeloid leukemia K562", 《INVEST NEW DRUGS》, vol. 30, 5 January 2011 (2011-01-05), pages 862 - 869 * |
| ROBERTB RUCEM OFFETTA, ET AL.: "Antiulcer Agents. p-Aminobenzamido Aromatic Compounds", 《JOURNAL OF MEDICINAL CHEMISTRY》, vol. 14, no. 10, 31 December 1971 (1971-12-31), pages 963 - 968 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108402064A (en) * | 2018-04-14 | 2018-08-17 | 张汝伟 | A kind of secondary amine derivative is applied with halosulfuronmethyl synergy and its herbicidal formulations |
| CN108432777A (en) * | 2018-04-14 | 2018-08-24 | 张汝伟 | A kind of secondary amine derivative combines the application in plant growth regulating with TrinexAN_SNacethyl |
| CN108432776A (en) * | 2018-04-14 | 2018-08-24 | 张汝伟 | A kind of composition comprising TrinexAN_SNacethyl and its application in plant growth regulating |
| WO2022008923A1 (en) | 2020-07-10 | 2022-01-13 | MOA Technology Limited | Herbicidal heterocyclic derivatives |
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